Product Name

  • Name

    3-(Aminomethyl)pyridine

  • EINECS 223-091-0
  • CAS No. 3731-52-0
  • Article Data72
  • CAS DataBase
  • Density 1.053 g/cm3
  • Solubility Freely soluble in water
  • Melting Point -21 °C(lit.)
  • Formula C6H8N2
  • Boiling Point 226 °C at 760 mmHg
  • Molecular Weight 108.143
  • Flash Point 100.6 °C
  • Transport Information UN 2735 8/PG 2
  • Appearance Clear colourless to slighly yellow liquid
  • Safety 26-36/37/39-45-25-36
  • Risk Codes Statements 34-37-36/37/38
  • Molecular Structure Molecular Structure of 3731-52-0 (3-(Aminomethyl)pyridine)
  • Hazard Symbols CorrosiveC, IrritantXi
  • Synonyms 3-Aminomethylpyridine;2-Aminomethyl pyridine;Pyridine, 3- (aminomethyl)-;Picolaminum [INN-Latin];pyridin-3-ylmethanamine;3-Pyridinemethanamine;Picolamine;Picolamine [DCF:INN];3-Picolylamine;3-Pyridylmethylamine;Pyridine, 3-(aminomethyl)- (8CI);Picolamina [INN-Spanish];pyridin-3-ylmethylazanium;1-pyridin-3-ylmethanamine;3-Pyridinemethylamine;
  • PSA 38.91000
  • LogP 1.24060

Synthetic route

pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry;99.9%
With palladium 10% on activated carbon; ammonia; hydrogen In methanol at 30℃; under 7500.75 Torr; for 4h; Reagent/catalyst; Temperature; Pressure; Autoclave;93.44%
With hydrogen; silica gel; nickel In methanol; ammonia at 120℃; under 7600 Torr; for 6h;86%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at 30℃; for 20h; Autoclave;97%
With N,N'-bis(salicylidene)-1,2-phenylene-diaminocobalt(II); ammonia; hydrogen In water at 120℃; for 24h; Autoclave;84%
Multi-step reaction with 2 steps
1: water; potassium carbonate; hydroxylamine hydrochloride
2: ethanol; zinc; acetic acid
View Scheme
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; for 20h; Inert atmosphere; Cooling;96%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; under 12001.2 Torr; for 20h; Inert atmosphere; Autoclave; chemoselective reaction;96 %Chromat.
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

ammoniacal methanol

ammoniacal methanol

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
85.6%
84.2%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

6-chloronicotinylaldehyde
23100-12-1

6-chloronicotinylaldehyde

C

bis(6-chloro-3-pyridylmethyl)amine

bis(6-chloro-3-pyridylmethyl)amine

D

5-(aminomethyl)-2-chloropyridine
97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 760 Torr; for 5h; Reduction;A 3%
B 5%
C 8%
D 75%
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 912 - 1064 Torr; for 9h; Product distribution; Further Variations:; Catalysts; Pressures; Temperatures; Reduction;A 2%
B 1%
C 2%
D 73%
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 912 - 1064 Torr; Reduction;A 2%
B 2%
C 2%
D 73%
With hydrogen; Raney Nickel R-100 In methanol; ammonium hydroxide at 25℃; under 760 Torr; for 9h; Product distribution; Further Variations:; Catalysts; Pressures; Solvents; Temperatures; Hydrogenation;A 11%
B 3%
C 17%
D 59%
...Expand
nicotinaldehyde oxime
51892-16-1

nicotinaldehyde oxime

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 0.5h; Ambient temperature;74%
With ethanol; acetic acid; zinc
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

bis(6-chloro-3-pyridylmethyl)amine

bis(6-chloro-3-pyridylmethyl)amine

C

5-(aminomethyl)-2-chloropyridine
97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 760 Torr; for 1.5h; Reduction;A 17%
B 3%
C 62%
...Expand
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

bis(pyridin-3-ylmethyl)amine
1656-94-6

bis(pyridin-3-ylmethyl)amine

Conditions
ConditionsYield
With 1,4-dioxane; nickel at 130℃; under 147102 Torr; Hydrogenation;
With ethanol; nickel at 130℃; under 147102 Torr; Hydrogenation;
With ammonia; nickel at 70 - 80℃; under 77228.3 Torr; Hydrogenation;
3-Methylpyridine
108-99-6

3-Methylpyridine

A

pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

B

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

C

carbon dioxide
124-38-9

carbon dioxide

D

nicotinamide
98-92-0

nicotinamide

Conditions
ConditionsYield
With ammonia; oxygen; vanadia at 375℃; Product distribution; other catalysts, effect of the presence of O2;
...Expand
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

chromium (II)-acetate

chromium (II)-acetate

aq.-ethanolic KOH-solution

aq.-ethanolic KOH-solution

hydrogen

hydrogen

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

...Expand
1,4-dioxane
123-91-1

1,4-dioxane

pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

Raney nickel

Raney nickel

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

bis(pyridin-3-ylmethyl)amine
1656-94-6

bis(pyridin-3-ylmethyl)amine

Conditions
ConditionsYield
at 130℃; under 147102 Torr; Hydrogenation;
...Expand
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

ethanol
64-17-5

ethanol

Raney nickel

Raney nickel

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

bis(pyridin-3-ylmethyl)amine
1656-94-6

bis(pyridin-3-ylmethyl)amine

Conditions
ConditionsYield
at 130℃; under 147102 Torr; Hydrogenation;
...Expand
nicotinic acid
59-67-6

nicotinic acid

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium acetate; acetic acid / Langsame Destillation des Reaktionsgemisches
2: Raney nickel; ethanol; dioxane / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: ammonium acetate; acetic acid / Langsame Destillation des Reaktionsgemisches
2: Raney nickel; ethanol / 130 °C / 147102 Torr / Hydrogenation
View Scheme
1,3,5-tris(pyridin-3-ylmethyl)-1,3,5-triazine
261958-73-0

1,3,5-tris(pyridin-3-ylmethyl)-1,3,5-triazine

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water
nicotinamide
98-92-0

nicotinamide

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With tris(2,4-pentanedionato)ruthenium(III); ytterbium(III) trifluoromethanesulfonate nonohydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; under 3750.38 Torr; for 15h; Autoclave;A n/a
B 11 %Chromat.
2-(3-pyridinylmethyl)-1H-isoindole-1,3(2H)-dione
34403-38-8

2-(3-pyridinylmethyl)-1H-isoindole-1,3(2H)-dione

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

phthalyl alcohol
612-14-6

phthalyl alcohol

Conditions
ConditionsYield
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 15001.5 Torr; for 24h; Autoclave;
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

A

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

B

nicotinamide
98-92-0

nicotinamide

Conditions
ConditionsYield
With ammonium hydroxide; chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen at 100℃; under 20686.5 Torr; for 24h; Autoclave; Green chemistry; chemoselective reaction;
C18H20N2Si2

C18H20N2Si2

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃;
3-pyridinealdoxime
1193-92-6

3-pyridinealdoxime

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
With hydrogenchloride; zinc In ethanol; dichloromethane; water for 2h;
C6H8N2*H(1+)

C6H8N2*H(1+)

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water
2: oxygen
3: hydroxylamine; hydrogenchloride / water; ethanol; dichloromethane / 2 h / 20 °C
4: hydrogenchloride; zinc / water; ethanol; dichloromethane / 2 h
View Scheme
C6H7NO*H4N(1+)

C6H7NO*H4N(1+)

3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: oxygen
2: hydroxylamine; hydrogenchloride / water; ethanol; dichloromethane / 2 h / 20 °C
3: hydrogenchloride; zinc / water; ethanol; dichloromethane / 2 h
View Scheme
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-<amino>methyl>pyridine
102297-41-6

3-<amino>methyl>pyridine

Conditions
ConditionsYield
In 1,4-dioxane for 3h; Ambient temperature;100%
With glycerol at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;96%
With sulfated tungstate 10 wt % In neat (no solvent) at 20℃; for 0.0833333h; chemoselective reaction;95%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

acetic anhydride
108-24-7

acetic anhydride

N-(pyridin-3-ylmethyl)acetamide
22977-34-0

N-(pyridin-3-ylmethyl)acetamide

Conditions
ConditionsYield
In water at 10 - 25℃; for 18h;100%
In tetrahydrofuran at 20℃; for 5h;85%
With pyridine; dmap for 92h; Ambient temperature;46%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

(E)-3-[(Pyridin-3-ylmethyl)-amino]-acrylic acid methyl ester

(E)-3-[(Pyridin-3-ylmethyl)-amino]-acrylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 5h; Ambient temperature;100%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

fenoxaprop-p-ethyl
66441-23-4, 71283-80-2

fenoxaprop-p-ethyl

A

(R)-2-(4-hydroxyphenoxy)propionic acid ethyl ester
71301-98-9

(R)-2-(4-hydroxyphenoxy)propionic acid ethyl ester

B

(6-chloro-benzooxazol-2-yl)-pyridin-3-yl-amine

(6-chloro-benzooxazol-2-yl)-pyridin-3-yl-amine

Conditions
ConditionsYield
at 20℃;A n/a
B 100%
...Expand
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

(2,2,5,7,8-pentamethylchroman-6-sulfonyl)isothiocyanate
773147-11-8

(2,2,5,7,8-pentamethylchroman-6-sulfonyl)isothiocyanate

C21H27N3O3S2
1061736-60-4

C21H27N3O3S2

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.25h;100%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Benzophenone imine
1013-88-3

Benzophenone imine

N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine
175441-83-5

N-(diphenylmethylene)-1-(pyridin-3-yl)methanamine

Conditions
ConditionsYield
at 50 - 60℃;100%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

benzaldehyde
100-52-7

benzaldehyde

(E)-N-phenylmethylene-1-(3-pyridyl)methanamine
1256973-71-3

(E)-N-phenylmethylene-1-(3-pyridyl)methanamine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Molecular sieve;100%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

ethyl 2-(2-amino-4,6-dichloropyrimidin-5-yl)acetate
848694-76-8

ethyl 2-(2-amino-4,6-dichloropyrimidin-5-yl)acetate

2-amino-4-chloro-7-(pyridin-3-ylmethyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one
1196886-72-2

2-amino-4-chloro-7-(pyridin-3-ylmethyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 120℃; for 12h; Inert atmosphere;100%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

salicylaldehyde
90-02-8

salicylaldehyde

N-salicylidene-3-(aminomethyl)pyridine
58199-72-7

N-salicylidene-3-(aminomethyl)pyridine

Conditions
ConditionsYield
In benzene for 24h; Reflux;99%
In benzene for 24h; Reflux;99%
In ethanol at 98℃; for 1h;92%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

2,4 dichlorobenzoic acid
50-84-0

2,4 dichlorobenzoic acid

potassium carbonate
584-08-7

potassium carbonate

4-Chloro-2-(pyridin-3-ylmethylamino)benzoic acid

4-Chloro-2-(pyridin-3-ylmethylamino)benzoic acid

Conditions
ConditionsYield
copper(I) bromide In N,N-dimethyl-formamide99%
...Expand
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

C23H15NO8

C23H15NO8

N-[4,8-etheno-8-(2-furyl)-1,3,5,7-tetraoxo-2,6-bis(3-pyridylmethyl)dodecahydropyrrolo[3,4-f]isoindol-4-yl]benzamide

N-[4,8-etheno-8-(2-furyl)-1,3,5,7-tetraoxo-2,6-bis(3-pyridylmethyl)dodecahydropyrrolo[3,4-f]isoindol-4-yl]benzamide

Conditions
ConditionsYield
In water at 160℃; for 0.833333h; microwave irradiation;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

2-isopropyl-1-(prop-2-yn-1-yl)-1H-indazol-3(2H)-one
1309979-75-6

2-isopropyl-1-(prop-2-yn-1-yl)-1H-indazol-3(2H)-one

2-isopropyl-1-((1-(pyridin-3-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)-1H-indazol-3(2H)-one

2-isopropyl-1-((1-(pyridin-3-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl)-1H-indazol-3(2H)-one

Conditions
ConditionsYield
Stage #1: 3-Aminomethylpyridine With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate In methanol at 20℃; for 24h;
Stage #2: 2-isopropyl-1-(prop-2-yn-1-yl)-1H-indazol-3(2H)-one With sodium L-ascorbate In methanol; water at 20℃; for 24h;		99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-2-methylacrylic acid
1321992-09-9

3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-2-methylacrylic acid

3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-2-methyl-N-(pyridin-3-ylmethyl)acrylamide
1321992-40-8

3-(2-(4-methoxybenzylamino)-6-bromoquinolin-3-yl)-2-methyl-N-(pyridin-3-ylmethyl)acrylamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetra fluoroborate; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 1h; Inert atmosphere;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Hexyl isocyanate
2525-62-4

Hexyl isocyanate

1-hexyl-3-(pyridin-3-ylmethyl)urea
1231764-78-5

1-hexyl-3-(pyridin-3-ylmethyl)urea

Conditions
ConditionsYield
In dichloromethane at 0℃; Reflux;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tertbutyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)acrylic acid
1417091-40-7

2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tertbutyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)acrylic acid

2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tertbutyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)-N-((pyridin-3-yl)methyl)acrylamide
1417091-43-0

2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tertbutyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)-N-((pyridin-3-yl)methyl)acrylamide

Conditions
ConditionsYield
Stage #1: 2E-3-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tertbutyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)acrylic acid With dmap; 2-methyl-6-nitrobenzoic anhydride at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 3-Aminomethylpyridine at 20℃; for 13h; Inert atmosphere;		99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

1-(pyridin-3-yl)-N-(pyridin-3-ylmethylene)methanamine
141136-36-9

1-(pyridin-3-yl)-N-(pyridin-3-ylmethylene)methanamine

Conditions
ConditionsYield
With oxygen In acetonitrile at 80℃; under 2250.23 Torr; for 5h; Autoclave;99%
With NC-800; air In water; dimethyl sulfoxide at 120℃; for 8h; Green chemistry;93%
With N,N-diallyl-2,3,5,6-tetramethylpyrazine; oxygen In neat (no solvent) at 100℃; for 16h; Schlenk technique;65%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride
129-64-6

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

(1α,2α,6α,7α)-4-(pyridin-3-ylmethyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

(1α,2α,6α,7α)-4-(pyridin-3-ylmethyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

Conditions
ConditionsYield
In toluene at 200℃; for 0.166667h;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

dimethyl (1α,2α,6α,7α,8β,11β)-3,5-dioxo-4-oxatetracyclo[5.4.1.02,6.08,11]dodec-9-ene-9,10-dicarboxylate
856244-88-7

dimethyl (1α,2α,6α,7α,8β,11β)-3,5-dioxo-4-oxatetracyclo[5.4.1.02,6.08,11]dodec-9-ene-9,10-dicarboxylate

dimethyl (1α,2α,6α,7α,8β,11β)-3,5-dioxo-4-(pyridin-3-ylmethyl)-4-azatetracyclo[5.4.1.02,6.08,11]dodec-9-ene-9,10-dicarboxylate

dimethyl (1α,2α,6α,7α,8β,11β)-3,5-dioxo-4-(pyridin-3-ylmethyl)-4-azatetracyclo[5.4.1.02,6.08,11]dodec-9-ene-9,10-dicarboxylate

Conditions
ConditionsYield
at 170℃; for 0.0833333h;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

phenylacetic acid
103-82-2

phenylacetic acid

2-phenyl-N-((pyridin-3-yl)methyl)acetamide
349404-17-7

2-phenyl-N-((pyridin-3-yl)methyl)acetamide

Conditions
ConditionsYield
With Cp2Zr(OTf)2•THF In tetrahydrofuran at 70℃; for 48h; Sealed tube; Inert atmosphere;99%
Stage #1: 3-Aminomethylpyridine; phenylacetic acid In methanol; water at 20℃; for 5h;
Stage #2: With N-tosylimidazole In N,N-dimethyl-formamide at 100℃; for 1h;
Stage #3: With triethylamine In N,N-dimethyl-formamide at 100℃;
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

N-(pyridine-2-yl)methylformamide
56625-04-8

N-(pyridine-2-yl)methylformamide

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With bis(2-chlorophenyl)borinic acid; acetic acid at 65℃; for 0.25h; Inert atmosphere;
Stage #2: 3-Aminomethylpyridine at 65℃; for 12h; Temperature; Inert atmosphere;		99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3-O-acetylbetulinic acid chloride
59868-82-5

3-O-acetylbetulinic acid chloride

(3β)-28-oxo-28-[(pyridin-3-ylmethyl)amino]lup-20(29)-en-3-yl acetate
917869-66-0

(3β)-28-oxo-28-[(pyridin-3-ylmethyl)amino]lup-20(29)-en-3-yl acetate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;99%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

isobutyraldehyde
78-84-2

isobutyraldehyde

isobutylidene-3-aminomethylpyridine

isobutylidene-3-aminomethylpyridine

Conditions
ConditionsYield
In toluene98.8%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

C6H9BF2O3

C6H9BF2O3

C10H11BF2N2O2

C10H11BF2N2O2

Conditions
ConditionsYield
In acetonitrile at 25℃;98%
In acetonitrile at 25℃; for 0.5h;95%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

4-fluorobenzoyl chloride
403-43-0

4-fluorobenzoyl chloride

4-Fluoro-N-(pyridin-3-ylmethyl)benzamide
333433-98-0

4-Fluoro-N-(pyridin-3-ylmethyl)benzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;98%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

4-(t-butylmercapto)phenyl isocyanate
54528-31-3

4-(t-butylmercapto)phenyl isocyanate

1-(pyridin-3-ylmethyl)-3-(4-t-butylmercaptophenyl)-urea

1-(pyridin-3-ylmethyl)-3-(4-t-butylmercaptophenyl)-urea

Conditions
ConditionsYield
In benzene98%
In benzene98%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

benzaldehyde
100-52-7

benzaldehyde

3-(benzylaminomethyl)pyridine dihydrochloride

3-(benzylaminomethyl)pyridine dihydrochloride

Conditions
ConditionsYield
With chloroform; 10% Pd/C; hydrogen In methanol at 20℃; under 760.051 Torr; for 3h; chemoselective reaction;98%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

nicotinamide
98-92-0

nicotinamide

Conditions
ConditionsYield
With manganese(IV) oxide at 130℃; under 4560.31 Torr; for 3h;98%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium tert-butylate In tert-butyl alcohol at 70℃; for 12h;96%
With oxygen; potassium carbonate; copper(I) bromide In water; dimethyl sulfoxide at 140℃; under 760.051 Torr; for 6h;90%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

(2E,4E)-5-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tert-butyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)-2-ethylpenta-2,4-dienoic acid
1417091-59-8

(2E,4E)-5-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tert-butyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)-2-ethylpenta-2,4-dienoic acid

(2E,4E)-5-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tert-butyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)-2-ethyl-N-((pyridin-3-yl)methyl)penta-2,4-dienamide
1417091-64-5

(2E,4E)-5-((3S,4S,4aS,5S,6S,7R,8aR)-3,4,4a,5,6,7,8,8a-octahydro-6-(tert-butyldimethylsiloxy)-3,5,7-trimethylnaphthalen-4-yl)-2-ethyl-N-((pyridin-3-yl)methyl)penta-2,4-dienamide

Conditions
ConditionsYield
With dmap; 2-methyl-6-nitrobenzoic anhydride at 20℃; for 13h; Inert atmosphere;98%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

(E)-1-(pyridin-3-yl)-N-(pyridin-3-ylmethylene)methanamine

(E)-1-(pyridin-3-yl)-N-(pyridin-3-ylmethylene)methanamine

Conditions
ConditionsYield
With C14H14N2(1+)*BF4(1-); oxygen In neat (no solvent) at 100℃; under 750.075 Torr; Schlenk technique;98%
With dihydrogen peroxide In water at 100℃; for 16h; Sealed tube;41 %Spectr.
With 1,5-diaminoanthraquinone; oxygen In [D3]acetonitrile at 30℃; for 24h; Solvent; Irradiation; Sealed tube;77 %Spectr.

3-(Aminomethyl)pyridine Chemical Properties

MF: C6H8N2
Synonyms: C-PYRIDIN-3-YL-METHYLAMINE;3-(AMINOMETHYL)PYRIDINE;3AMPY;3-PYRIDINEMETHANAMINE;3-PYRIDYLMETHYLAMINE;3-PICOLYLAMINE;AKOS BBS-00003679;Picolamine
MW: 108.14
EINECS: 223-091-0
mp : ?21 °C(lit.)
bp : 73-74 °C1 mm Hg(lit.)
density : 1.062 g/mL at 25 °C(lit.)
refractive index : n20/D 1.551(lit.)
Fp : 213 °F
Water Solubility : FREELY SOLUBLE
BRN : 108056

3-(Aminomethyl)pyridine Safety Profile

Risk Statements : 34-37-36/37/38
Safety Statements :26-36/37/39-45-25-36
Hazard Codes : C,Xi
RIDADR : UN 2735 8/PG 2
WGK Germany : 3
Hazard Note :Irritant
HazardClass : 8
PackingGroup : III
HS Code : 29333999

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